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Search results; Over 1,000 homes in Montepulciano

Top guest favorite
Frescoed ceilings and 180° valley views greet you at this Montepulciano flat
2 bedrooms, 5 beds, 1 private bath
Oct 4 – 9
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4.93 out of 5 average rating, 153 reviews
Top guest favorite
Wooden beams, stone walls, and a fireplace greet you at this Montepulciano loft
5.0 out of 5 average rating, 508 reviews, 2 beds, 1 bath
Aug 14 – 19
Top guest favorite
A 17th century Tuscan-style apartment in Montepulciano with a cinema room
5.0 out of 5 average rating, 212 reviews, 1 bedroom, 3 beds, 2 baths
Oct 30 – Nov 4
Top guest favorite
Look out over Val d’Orcia from your terrace at this Montepulciano condo
5.0 out of 5 average rating, 128 reviews, 1 bedroom, 1 bed, 1 bath
Nov 3 – 8
Top guest favorite
This 500-year-old house on 33 private acres gives you a pool and Tuscan hills
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 3 baths
Oct 26 – 31
Top guest favorite
Soak in hilltop views from the hot tub at this Chianciano Terme villa
4.97 out of 5 average rating, 127 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 13 – 18
Top guest favorite
Look out over a historic square and countryside from this San Quirico condo
4.99 out of 5 average rating, 98 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 1 – 6
Top guest favorite
This Montepulciano villa nestles you among vineyards with a private pool and hot tub
4.97 out of 5 average rating, 123 reviews, 4 bedrooms, 5 beds, 2.5 baths
Nov 15 – 20
Top guest favorite
Infinite valley views greet you at this Chiusi guesthouse with a private pool
4.97 out of 5 average rating, 238 reviews, 1 bedroom, 2 beds, 1 bath
Oct 30 – Nov 4
Top guest favorite
Look out over the Crete Senesi from this Asciano condo’s hilltop garden
4.98 out of 5 average rating, 320 reviews, 2 bedrooms, 4 beds, 1 bath
Oct 26 – 31
Guest favorite
This spacious Montepulciano apartment puts you in the historic center among boutiques and wineries
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1.5 baths
Sep 26 – Oct 1
Top guest favorite
Wake to Val d’Orcia views from this vineyard-surrounded San Quirico farmstay
4.98 out of 5 average rating, 115 reviews, 5 bedrooms, 5 beds, 5.5 baths
Aug 30 – Sep 4
Top guest favorite
This Pienza apartment puts you in a mid-1400s building with Val d’Orcia views
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Top guest favorite
Exposed beams and a private courtyard greet you at this Montepulciano apartment
4.91 out of 5 average rating, 77 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
Look out over Tuscan hills from this Montepulciano apartment’s terrace
4.97 out of 5 average rating, 322 reviews, 2 bedrooms, 3 beds, 2 baths
Nov 15 – 20
Top guest favorite
This 18th-century Siena duplex gives you countryside views and original ceiling beams
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Top guest favorite
Look out over the walls from this top-floor Montepulciano apartment in a historic palace
4.99 out of 5 average rating, 301 reviews, 1 bedroom, 2 beds, 1 bath
Nov 8 – 13
Guest favorite
This quiet Pienza villa gives you a private backyard near the historic center
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 1 bed, 3 baths
Sep 17 – 22
Top guest favorite
A 1000-year-old tower in San Quirico d’Orcia where you’ll overlook Val d’Orcia
5.0 out of 5 average rating, 114 reviews, 1 bedroom, 1 bed, 1 bath
Aug 24 – 29